Cited by 146Asymmetric Synthesis and CatalysisSynthesis of Indole DerivativesAsymmetric Hydrogenation and Catalysis

Recent catalytic asymmetric syntheses of 3,3-disubstituted indolin-2-ones and 2,2-disubstituted indolin-3-ones

Dalpozzo, Renato·2017·Advanced Synthesis & Catalysis

Abstract

Abstract Disubstituted oxindoles represent an important family of bioactive compounds and synthetic derivatives that mimic natural products. The construction of the asymmetric quaternary carbon at C‐3 or C‐2 is therefore a challenging problem for organic chemists. In the last years, many papers have appeared on asymmetric catalytic methods for the synthesis of these compounds, in particular about spirocyclic derivatives and this literature has been largely reviewed, as well as the literature on 3‐substituted‐3‐hydroxyoxindoles and 3‐substituted‐3‐aminooxindoles. On the other hand, the literature on non‐spirocyclic 3,3‐dialkyloxindoles as well as on 2,2‐disubstituted 3‐indolinones has not fully reviewed since our previous review on this topic. This review aims to fill this gap covering the literature on these topics. Abbreviations: Alloc=allyloxycarbonyl; Ant=anthracenyl; BINOL=1,1′‐binaphthalene‐2,2′‐diol; Boc=t‐butoxycarbonyl; Bz=benzoyl; Cbz=benzyloxycarbonyl; CSA=camphorsulfonic acid; Cy=cyclohexyl; DABCO=1,4‐diazabicyclo[2.2.2]octane; dba=bis(dibenzylideneacetone); DBU=1,8‐diazabicyclo[5.4.0]undec‐7‐ene; DDQ=2,3‐dichloro‐5,6‐dicyano‐1,4‐benzoquinone; (DHQD)2AQN=hydroquinidine (anthraquinone‐1,4‐diyl) diether; (DHQD)2PHAL=hydroquinidine 1,4‐phthalazinediyl diether; (DHQD)2PYR=hydroquinidine 2,5‐diphenyl‐4,6‐pyrimidinediyl diether; DIPEA=N,N‐diisopropylethylamine; esp=α,α,α′,α′‐tetramethyl‐1,3‐benzenedipropionic acid; HFIP=1,1,1,3,3,3‐hexafluoro‐2‐propanol; HMDS=hexamethyldisilazane; β‐ICD=β‐isocupreidine; LG=leaving group; Mes=2,4,6‐trimethylphenyl; Moc=methoxycarbonyl; MOM=methoxymethyl; MS=molecular sieves; MsOH=methanesulfonic acid; NHC=N‐heterocyclic carbene; Npt=naphthyl; PG=protecting group; Phg=phenylglycine; Phth=phthalimidyl; Piv=2,2‐dimethylpropanoyl; PMB=4‐methoxybenzyl; Red‐Al=sodium bis(2‐methoxyethoxy)aluminium hydride; Suc=succinimidyl; TBDPS=tert‐butyldiphenylsilyl; TBS=tert‐butyldimethylsilyl; TES=triethylsilyl; TIPS=triisopropylsilyl; TMEDA=N,N,N′,N′‐tetramethylethylenediamine; TMG=1,1,3,3‐tetramethylguanidine; TMS=trimethylsilyl; Ts=4‐toluenesulfonyl. magnified image

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Crossref · 10.1002/adsc.201700361

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Authors
Dalpozzo, R.
Affiliations
University of Calabria (IT)
Corresponding author
Dalpozzo, Renato
Venue
Advanced Synthesis & Catalysis
Publisher
Wiley
Published
2017-05-19
Volume
359
Issue
11
Pages
1772-1810
ISSN
  • 1615-4150 (ISSN-L)
  • 1615-4169
OpenAlex
W2607228692
Cited by
146
References
157
Citations by year
2026: 10 · 2025: 6 · 2024: 15 · 2023: 22 · 2022: 10 · 2021: 14 · 2020: 19 · 2019: 17 · 2018: 30 · 2017: 3
FWCI
7.89
Type
journal article
Language
en
Open access
closed
Locations
  • Advanced Synthesis & Catalysis (publishedVersion)
  • Archive of Doctoral Theses and Digital Collections (University of Calabria) (submittedVersion)
Topics
  • Physical Sciences › Chemistry › Organic Chemistry › Asymmetric Synthesis and Catalysis
  • Physical Sciences › Chemistry › Organic Chemistry › Synthesis of Indole Derivatives
  • Physical Sciences › Chemistry › Inorganic Chemistry › Asymmetric Hydrogenation and Catalysis
Keywords
asymmetric catalysis, oxindoles, indolin-3-ones

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